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Jake's Tips for What to Wear on a First Date

I'm here to help you navigate the sometimes impenetrable, inscrutable male mind and make dating a more pleasant and hopefully more fruitful experience. So please feel free to ask me anything via Twitter at @glamour_jake or via email smittenbloggers@gmail.com.

Hi Jake,

I haven't been in a relationship for three years, and I like it except when my parents keeping saying to just find a man and get married. Recently I hit on a man who I think is really into my type, and we really get into a long conversations—though we haven't met yet. We're going on a blind date, so should I behave restrained, shy, and reserved when I meet him? Or should I really start using makeup and get myself "like a butterfly" to attract him?

Hi,

I don’t think you should try to behave a certain kind of way or pretend to be something you’re not. These three words may sound cliche, but they are totally true: Just be yourself.

Now, this is not to say you can’t doll yourself up a bit for the date—I just wouldn’t dress up like someone that’s not you. If you’re most comfortable in a cute T-shirt and jeans, then wear that! You don’t have to try to be overly sexy or anything, and when it comes to makeup, personally, I don’t like noticing when a girl is wearing makeup. To me, the best kind of makeup is when I can’t tell she’s wearing it. Otherwise, it makes me think she’s trying to hide what she really looks like.

If you’ve been texting for a while, just be careful that his (and your) expectations are not so high going into it that once you meet, it’s a disappointment. People are often very different in the flesh!

Best of luck! —Jake

For more advice, download Glamour's digital edition or pick up an issue on newsstands now. P.S. Do you have dating or relationship questions for Jake? Ask in the comments below, tweet him @glamour_jake, or email smittenbloggers@gmail.com.